Best overall
Tipsy History Tour: 300+ Years of Annapolis Drinking History
Highest Outty Ranking in the city right now.
Outty Ranking 79 · from $39
Things to do in Annapolis, compared
We rank 35 experiences in Annapolis, United States, and compare the top 20 on ranking, price, length, and traveler rating. The strongest overall is Tipsy History Tour: 300+ Years of Annapolis Drinking History at 79 out of 100, the lowest entry price is $6 per person, and 0 experiences sit in the Outty 90+ Club. Traveler ratings shown here are provided by Viator and Tripadvisor.
Which one should you book?
Best with kids
Annapolis Historic Walking Tour: Harbor and Colonial Downtown
Top ranked experience the operator lists as family friendly.
Outty Ranking 71 · from $235
Most proven
Ashes and Apparitions of Annapolis Ghost Tour
The deepest traveler review history of anything we rank here.
Outty Ranking 65 · from $26
Full comparison
| Experience | Outty Ranking | Verdict | From | Duration | Traveler rating | Cancellation |
|---|---|---|---|---|---|---|
| Tipsy History Tour: 300+ Years of Annapolis Drinking History | 79 | Strongly Recommended | $39 | 2h | 5.0/5 (47) | Free to 24h before |
| Historic Annapolis Food Tour | 72 | Strongly Recommended | $80 | 3.5h | 4.7/5 (49) | Free to 24h before |
| Annapolis Historic Walking Tour: Harbor and Colonial Downtown | 71 | Strongly Recommended | $235 | 1.8h | 5.0/5 (47) | Free to 24h before |
| Historic Annapolis Walking Tour - Small Group Guided Tour | 68 | Solid Choice | $35 | 1.5h | 4.9/5 (19) | Free to 24h before |
| The Original Walking Ghost Tour by Annapolis Ghost Tours | 67 | Solid Choice | $26 | 1.5h | 4.4/5 (49) | Free to 24h before |
| The Original Haunted Pub Crawl by Annapolis Ghost Tours | 66 | Solid Choice | $31 | 2h | 4.5/5 (23) | Free to 24h before |
| Ashes and Apparitions of Annapolis Ghost Tour | 65 | Solid Choice | $26 | 1h | 4.3/5 (91) | Free to 24h before |
| Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl | 62 | Solid Choice | $29 | 2h | 4.4/5 (15) | Free to 24h before |
| Best of Annapolis Tour: Colonial, State House, Naval Academy | 62 | Solid Choice | $34 | 2.3h | 4.5/5 (11) | Free to 24h before |
| Annapolis Harbor and U.S. Naval Academy Cruise | 60 | Worth a Look | $34 | 0.7h | 4.8/5 (16) | Free to 24h before |
| Annapolis Colonial and Maritime History Walking Tour | 59 | Worth a Look | $49 | 2h | 4.6/5 (11) | Free to 24h before |
| Amazing Annapolis Scavenger Hunt | 58 | Worth a Look | $20 | 2h | 4.1/5 (8) | Free to 24h before |
| Annapolis Thomas Point Lighthouse Cruise | 55 | Worth a Look | $46 | 1.5h | 4.7/5 (7) | Free to 24h before |
| Colonial Annapolis and Maryland State House Walking Tour | 55 | Worth a Look | $26 | 1.5h | 5.0/5 (2) | Free to 24h before |
| Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views | 54 | Worth a Look | $15 | 2h | 3.7/5 (18) | Free to 24h before |
| Day on the Bay Cruise from Annapolis to St Michaels | 53 | Worth a Look | $157 | 8h | 4.3/5 (3) | Free to 24h before |
| Hidden History Pub Crawl of Historic Annapolis | 52 | Worth a Look | $30 | 2h | 5.0/5 (1) | Free to 24h before |
| Annapolis Chesapeake Bay Bridge Cruise | 51 | Worth a Look | $46 | 1.5h | 5.0/5 (2) | Free to 24h before |
| Annapolis Murder Mystery Self Guided City Detective Game | 50 | Worth a Look | $6 | 1.5h | Not yet rated | Free to 24h before |
| Spirits and Spirits Haunted Walking Tour and Boat Cruise | 50 | Worth a Look | $52 | 1.5h | 5.0/5 (2) | Free to 24h before |
Traveler ratings and review counts are provided by Viator and Tripadvisor. The Outty Ranking is our own evaluation and is calculated independently of them.